CA2655360C - Copolymeres reticulables par voie actinique pour la fabrication de lentilles de contact - Google Patents
Copolymeres reticulables par voie actinique pour la fabrication de lentilles de contact Download PDFInfo
- Publication number
- CA2655360C CA2655360C CA2655360A CA2655360A CA2655360C CA 2655360 C CA2655360 C CA 2655360C CA 2655360 A CA2655360 A CA 2655360A CA 2655360 A CA2655360 A CA 2655360A CA 2655360 C CA2655360 C CA 2655360C
- Authority
- CA
- Canada
- Prior art keywords
- hydrophilic monomer
- alkyl
- prepolymer
- group
- transfer agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000000178 monomer Substances 0.000 claims abstract description 137
- 125000000524 functional group Chemical group 0.000 claims abstract description 69
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 58
- 239000004971 Cross linker Substances 0.000 claims abstract description 57
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- 150000002894 organic compounds Chemical class 0.000 claims abstract description 41
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 40
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 28
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 26
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- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 20
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- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000000746 purification Methods 0.000 claims description 15
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical class 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001153 fluoro group Chemical class F* 0.000 claims description 3
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
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- 229920002554 vinyl polymer Polymers 0.000 description 27
- 238000004132 cross linking Methods 0.000 description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 25
- 238000000465 moulding Methods 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
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- 238000002360 preparation method Methods 0.000 description 18
- 230000005855 radiation Effects 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 15
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 15
- 230000035699 permeability Effects 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000004205 dimethyl polysiloxane Substances 0.000 description 12
- 238000003760 magnetic stirring Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 12
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 11
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 11
- 239000012530 fluid Substances 0.000 description 11
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 229960004592 isopropanol Drugs 0.000 description 11
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 11
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 11
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- 230000007717 exclusion Effects 0.000 description 10
- 238000000605 extraction Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
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- 238000000576 coating method Methods 0.000 description 9
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- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07C67/00—Preparation of carboxylic acid esters
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2483/04—Polysiloxanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Prostheses (AREA)
Abstract
L'invention porte sur de nouveaux copolymères réticulables qui peuvent être obtenus par (a) copolymérisation d'au moins deux monomères hydrophiles différents choisis dans le groupe constitué par le N,N-diméthyl acrylamide (DMA), l'acrylate de 2-hydroxyéthyle (HEA), le méthacrylate de glycidyle (GMA), la N-vinylpyrrolidone (NVP), l'acide acrylique (AA) et un (méth)acrylate d'alcoxy en C1-C4 polyéthylène glycol ayant une masse moléculaire moyenne en poids de 200 à 1.500, et au moins un réticulant comprenant deux doubles liaisons à insaturation éthylénique, ou davantage, en présence d'un agent de transfert de chaîne ayant un groupe fonctionnel; et (b) réaction d'un ou plusieurs groupes fonctionnels du copolymère résultant avec un composé organique ayant un groupe à insaturation éthylénique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83028806P | 2006-07-12 | 2006-07-12 | |
| US60/830,288 | 2006-07-12 | ||
| PCT/US2007/073119 WO2008008752A2 (fr) | 2006-07-12 | 2007-07-10 | Nouveaux polymères |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2655360A1 CA2655360A1 (fr) | 2008-01-17 |
| CA2655360C true CA2655360C (fr) | 2014-09-16 |
Family
ID=38670841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2655360A Expired - Fee Related CA2655360C (fr) | 2006-07-12 | 2007-07-10 | Copolymeres reticulables par voie actinique pour la fabrication de lentilles de contact |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US8404783B2 (fr) |
| EP (1) | EP2038310B1 (fr) |
| JP (1) | JP5271902B2 (fr) |
| CN (1) | CN101490099B (fr) |
| AR (1) | AR061978A1 (fr) |
| AT (1) | ATE470681T1 (fr) |
| AU (1) | AU2007272558B2 (fr) |
| BR (1) | BRPI0714430A2 (fr) |
| CA (1) | CA2655360C (fr) |
| DE (1) | DE602007007082D1 (fr) |
| DK (1) | DK2038310T3 (fr) |
| ES (1) | ES2346812T3 (fr) |
| MX (1) | MX2009000316A (fr) |
| NO (1) | NO340147B1 (fr) |
| PL (1) | PL2038310T3 (fr) |
| PT (1) | PT2038310E (fr) |
| TW (1) | TWI441835B (fr) |
| WO (1) | WO2008008752A2 (fr) |
| ZA (1) | ZA200810050B (fr) |
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-
2007
- 2007-07-10 PT PT07812745T patent/PT2038310E/pt unknown
- 2007-07-10 AT AT07812745T patent/ATE470681T1/de active
- 2007-07-10 EP EP07812745A patent/EP2038310B1/fr not_active Not-in-force
- 2007-07-10 CN CN2007800259565A patent/CN101490099B/zh not_active Expired - Fee Related
- 2007-07-10 ES ES07812745T patent/ES2346812T3/es active Active
- 2007-07-10 BR BRPI0714430-0A patent/BRPI0714430A2/pt not_active IP Right Cessation
- 2007-07-10 PL PL07812745T patent/PL2038310T3/pl unknown
- 2007-07-10 MX MX2009000316A patent/MX2009000316A/es active IP Right Grant
- 2007-07-10 AU AU2007272558A patent/AU2007272558B2/en not_active Ceased
- 2007-07-10 DK DK07812745.3T patent/DK2038310T3/da active
- 2007-07-10 JP JP2009519625A patent/JP5271902B2/ja not_active Expired - Fee Related
- 2007-07-10 CA CA2655360A patent/CA2655360C/fr not_active Expired - Fee Related
- 2007-07-10 TW TW096124986A patent/TWI441835B/zh not_active IP Right Cessation
- 2007-07-10 US US11/825,961 patent/US8404783B2/en active Active
- 2007-07-10 WO PCT/US2007/073119 patent/WO2008008752A2/fr not_active Ceased
- 2007-07-10 DE DE602007007082T patent/DE602007007082D1/de active Active
- 2007-07-12 AR ARP070103102A patent/AR061978A1/es not_active Application Discontinuation
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2008
- 2008-11-26 ZA ZA200810050A patent/ZA200810050B/xx unknown
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2009
- 2009-02-10 NO NO20090637A patent/NO340147B1/no not_active IP Right Cessation
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2013
- 2013-02-27 US US13/778,882 patent/US8703875B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101490099A (zh) | 2009-07-22 |
| NO20090637L (no) | 2009-03-31 |
| DK2038310T3 (da) | 2010-09-27 |
| ES2346812T3 (es) | 2010-10-20 |
| NO340147B1 (no) | 2017-03-13 |
| CN101490099B (zh) | 2013-03-27 |
| US8703875B2 (en) | 2014-04-22 |
| CA2655360A1 (fr) | 2008-01-17 |
| PT2038310E (pt) | 2010-08-25 |
| AU2007272558B2 (en) | 2010-12-09 |
| AU2007272558A1 (en) | 2008-01-17 |
| AR061978A1 (es) | 2008-08-10 |
| US8404783B2 (en) | 2013-03-26 |
| WO2008008752A3 (fr) | 2008-02-28 |
| MX2009000316A (es) | 2009-01-26 |
| EP2038310B1 (fr) | 2010-06-09 |
| JP2009543901A (ja) | 2009-12-10 |
| TW200821332A (en) | 2008-05-16 |
| US20080015315A1 (en) | 2008-01-17 |
| PL2038310T3 (pl) | 2010-11-30 |
| ATE470681T1 (de) | 2010-06-15 |
| WO2008008752A2 (fr) | 2008-01-17 |
| EP2038310A2 (fr) | 2009-03-25 |
| BRPI0714430A2 (pt) | 2013-03-12 |
| ZA200810050B (en) | 2009-12-30 |
| TWI441835B (zh) | 2014-06-21 |
| DE602007007082D1 (de) | 2010-07-22 |
| JP5271902B2 (ja) | 2013-08-21 |
| US20130172600A1 (en) | 2013-07-04 |
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